The Day the Music Died
by MoniNicole94
Summary: In 1959, a plane crash tragically took the lives of three musicians and their pilot. But the mysterious circumstances send the Winchester brothers on an adventure. Now they have a mystery to solve…before one of them joins the other three. (Warnings will be in each chapter)
1. Chapter 1

**AN: So I hope I can post this here. If not, just let me know. There are deaths in this first chapter, but they actually died in real life like 60 years ago... and this is fictionalized aspects of a real life event...**

 **1959**

The snow was blowing around the plane as the three musicians climbed aboard, rubbing their hands together to get the feeling back in them. Rockstar life was supposed to be easy street. How the hell did Elvis make it look so easy? But this flight would give the three of them a few hours to rest and get their heads together before they stood out in front of a crowd again.

"I hate winter." The seventeen-year-old said as he took his seat and bundled his jacket around him, shivering. "Pacoima? No snow. Warm. I love it."

"Not much different for us, you know." The twenty-eight-year-old said, taking his seat across from the kid. The third man set down by the twenty-eight-year-old, wiping snowflakes off his thick-rimmed glasses.

"Lubbock gets snow guys." He put his glasses back on his head. "And I thought that Sabine Pass got some too."

"I'm just saying that there's no snow in the valley." All three of them laughed, smiles on their faces.

"So, is Maria excited to have you back Holly?" The older man asked. The man he was speaking to was none other than Buddy Holly, the twenty-two-year-old heartthrob.

"Man, I miss her so much." Buddy laughed. "What about you two? Got anyone special waiting for you after the tour is over with?"

"Adrienne and my daughter." The older man, JP Richardson, also known as The Big Bopper, explained with a fond smile. "And Adrienne and I are having another one soon. You don't know how excited I am. I hope it's a boy." He looked over at the youngest one. "What about you Ritchie?"

"Just my family back in California." Ritchie Valens told his two flight mates. "This is the first time I've gone on a trip without them. I'm a little nervous about all of this. Kinda wish Dion would've just kept his spot." The Big Bopper reached across and slapped him on the knee.

"Relax Rich. Flying is perfectly safe. We're fine." He smiled at Ritchie then looked over at Buddy, who wasn't quite making eye contact with them. "Come on Holly. Help me put the kid's fears at ease."

"Oh, uh, yeah. He's right." Buddy said, nervously tapping his fingers on his thigh. "When are we taking off?"

"Anxious to get going?" The Big Bopper asked. Buddy nodded.

"Something like that." He said. Ritchie looked out the window at all the snow. It was like living in one of those snowglobes his sisters had. The plane jerked forward as it started to move down the runway. "Finally." He mumbled under his breath. He looked over at the Big Bopper. "So, Jiles, I had a question for you."

"Go ahead Holly. But you know you could call me JP or something like that." The Big Bopper laughed.

"Where were you ten years ago?" Buddy asked. The Big Bopper's smile fell. Ritchie looked at him.

"JP? What's wrong?" Ritchie asked.

"Yeah JP, what's wrong?" Buddy asked, a smirk on his face.

"Why would you ask that?" JP asked. Buddy started laughing.

"Well, I want to make sure I'm taking the right Jiles Perry Richardson with me." Buddy said, turning to look at the other man. The eyes underneath those thick-rimmed glasses turned as black as the night, making the Big Bopper and Ritchie jump out of their seats. "What's wrong guys? Something wrong with my face?"

"What is going on?" Ritchie asked, fear creeping into his voice.

"The Big Bopper here sold his soul." Buddy laughed. "Ten years is up Jiles. I wanted to handle this one myself. And behold, three young talents on a small plane."

"He did what?" Ritchie asked. "And why are your eyes black?!"

"I'm what you would call an uninvited guest." Buddy laughed. "A demon. And before you ask what happened to Buddy Holly, well," The demon moved Buddy's jacket aside, showing a darkening red spot on his low side. "He's been dead for a little while now."

"Oh Dios mas." Ritchie mumbled, making a cross over his chest. Buddy just laughed.

"He's not going to help you now." Buddy said, pushing Ritchie into his seat. "He's not going to help any of you anytime soon."

"You can't do this!" The Big Bopper called out. Buddy looked him straight in the eyes.

"You should've thought of that before you sold your soul." Buddy said. With that, he made his way to the cockpit, arguing with the pilot for a bit. The plane bounced around a bit, throwing Ritchie and the Big Bopper around before it headed down in a nosedive.


	2. Chapter 2

**AN: This is set in season 8. Thank you for the feedback I've been getting. It keeps me going!**

 **Present Day**

Blacktop rolled underneath the Impala as Sam and Dean made their way out of Kansas. There was an obvious chill in the air, and the clouds looked like there could be snow soon, but so far nothing. Dean was fine with that. He was never big on snow, especially when he had to be out in it during a hunt when he was younger. Sam was looking through something on his phone while Dean had his eyes glued to the road.

"Why Iowa?" Dean asked. Sam looked over at him.

"What?" He asked.

"Why are we going to Iowa? Like, aren't there other hunters in the midwest that can take on a ghost hunt?" Sam just shrugged, looking back at his phone.

"I just thought a normal ghost hunt would help us out some." He said. Dean smirked some.

"Normal ghost hunt. That's not something you hear every day." Dean glanced over at Sam. "But don't we have bigger things to worry about?"

"Like the trials?" Sam asked. Dean nodded. "We're waiting on Kevin. We don't know what the next step is." Dean sighed.

"And you're feeling okay, right?" He asked. Since Sam had covered himself in hellhound blood and taken on the task of closing the gates of Hell, Dean was starting to see Sam coughing a little more than normal and sleeping a little longer. But being a Winchester, Sam was stubborn as hell and wasn't about to tell Dean he was feeling run down.

"I'm fine." Sam finally said, hoping to satisfy Dean's questioning about that for the time being.

"So, ghost in Iowa?" Dean asked. Sam nodded.

"Uh yeah. Garth didn't give me a whole lot to go on except ghost terrorizing people." Sam explained.

"Garth put you on this lead?" Dean asked.

"Yeah. Said he's too busy tracking "hippie vamps" to take on the ghost right now. Thought we'd be the best to handle it."

"Well, he got that one right." Dean smirked. "Wait, did you say hippie vampires?"

"Yeah. Word for word. VW bus and everything." Sam told Dean. Dean sighed.

"Monsters man." He said. Sam nodded in agreement. "So, you doing research over there or reading your Hunger Games fanfiction?" It took Sam a second, but once he realized what Dean had said, he turned and glared at him.

"Research Dean." He growled. "I'm thinking it's a poltergeist. But we obviously can do more once we get there."

"Oh good. A blind hunt." Dean said. Sam sighed and went back to his phone. He was researching the town of Clear Lake, Iowa. There were a few news stories here and there about ghost hauntings, since the late 1950's. Either no hunter thought it was bad enough to deal with it, or no hunter could stop it.

But they needed this. They needed to get their minds on other things, instead of sitting around waiting for Kevin to unlock the next piece or Crowley to attack. The silence of the car was letting Sam think about all these things. Like what was the next trial going to be? Was it going to affect him worse than the first one did? Dean knew what Sam was thinking though, because he reached over to the volume knob on the radio.

"Too quiet in here." Dean said aloud. He knew that in the silence, Sam was going deep in his head, and that usually wasn't a good thing. He turned up the radio and listened to the song that came on.

 _Donna, where can you be?_

 _Where can you be?_

"What is this?" Dean asked, his nose turning up in disgust. "This isn't the classic rock station."

"I think it is." Sam said. "It's Ritchie Valens."

"Why are they playing him on here?" Dean asked. "Classic rock is Aerosmith. AC/DC. Not Ritchie Valens."

"I dunno man. I think Buddy Holly and all of them classify more as classic rock." Dean looked over at Sam like he had just committed the ultimate sin. "What?"

"I have half a mind to make you walk to Iowa." Dean growled. "Help me find a new station or something." Sam just smiled a bit before looking back at his phone. "Do you have anything or are you just using your phone as an excuse?"

"The ghost seems to be haunting the whole town." Sam explained, scrolling through something. "It moves around from place to place, throwing chairs, upending tables, things like that. It just recently got violent though. Almost like it's starting to get desperate for attention or something."

"A haunted town. Well this is going to be so much fun." He looked at the radio again.

 _Oh, Donna, oh, Donna_

"This is going to be a long freakin' drive."


	3. Chapter 3

**Warnings: Minor violence I think? Minor language.**

 **1959**

The crowd was full of energy as the man on the stage played his heart out for them. The girls screamed and cried. He was smiling as he watched everyone in the crowd. Buddy Holly was the crowd's favorite, it was obvious. He didn't know how he had gotten so lucky.

Buddy Holly, Waylon Jennings, Tommy Allsup, and Carl Bunch were rocking the crowd while the other acts relaxed around the building. Buddy couldn't stop smiling as he played through the songs he had been singing for the past couple years. It wasn't the Ed Sullivan show, but at least the production value wasn't so high that he was sick with nerves. And he had promised that Valens kid a good time on the tour.

Out in the crowd, a young man sat at a table. He sipped on his beer and watched the crowd. He would glance up at the band performing. Buddy was good, and if the man in the crowd didn't know better, he would've thought he sold his soul for fame and talent. But he hadn't. He was just actually good. The man's eyes drifted over to another man though. He was eating at a table with some other guys, instruments sitting around them.

His boss had given him orders to follow, and he as going to follow them. He just was going to do it with style.

Buddy and his band finished playing, taking their leave. His band mates headed for the bar. He took a moment to drink some water. He thought about trying to make a call to his dear Maria. It was quiet backstage and he could finally catch up with his thoughts. He took off his glasses and closed his eyes to relax for a bit.

"Excuse me, Mr. Holly?" A voice said. Buddy put his glasses back on and examined the person standing in front of him.

"Yes?" Buddy asked.

"My name is Corson. I'm a huge fan." He said with a smile.

"Oh, thanks. If you don't mind though, I am just about to make a call to my wife…" Buddy said. Instead, Corson set across from him.

"My boss sent me here. And boy I'm glad he did." Corson laughed, seeing the confusion on Buddy's face. "His name is Crowley. He's a real hard ass, but he has deadlines to meet and his boss is breathing down his neck."

"Are you a reporter or something?" Buddy asked. Corson smiled.

"Or something." He said. "Now, Mr. Holly, I think you can help me out." His eyes flashed black, making Buddy fall out of his chair in surprise.

"What are you?" Buddy asked. Corson stood up and laughed, towering over the musician as he laid on the floor.

"I'm just a working class stiff just trying to make it." Corson laughed. He grabbed Buddy by his shirt and pulled him up. "And I think you're going to help me out just fine. Too bad though. You won't be able to see that pretty little thing's face when she tells you that she's pregnant." Buddy's eyes widened. "Don't worry, it is yours. I visited her before I came here. She's just fine...for now."

"Leave Maria out of this!" Buddy snapped, but Corson grabbed him by his neck.

"You just save those vocals. You'll need them."

"What. Are. You." Buddy gasped. Corson laughed.

"See, where I come from, I'm just a simple grunt demon that does the dirty work of gathering souls. But here on earth, I'm Buddy Holly." With that, a black smoke left Corson's body and entered Buddy's despite him trying to keep his mouth shut to keep anything out. The body of the other man fell down, groaning some. Buddy stood up and dusted his suit off, before heading to the bar to get something to drink.

 **Present**

Dean pulled Baby into the parking lot of the Hilltop motel several hours later. They needed to set up a base camp, and Sam was so glad to be out of the car to stretch his long legs. Sam got out and stood by the car while Dean went to the office to get them a room. The sky was clear for now, but according to his phone, it was supposed to snow. Sam looked up then as Dean made his way to him.

"All the way on the end. In case any unwelcome visitors decide to show up in the dead of the night." Dean said. Sam nodded and got back into the car. Dean drove down to the end and parked so they could unload the bags. They knew the drill like the back of their hand. Check the room, lay some salt, make some sigils, the whole nine yards. Only once that was done could the boys settle down. Dean flopped down on his bed, relaxing so his back could find some relief, while Sam went to the yellowed Formica table and set up his laptop.

"What are you doing?" Dean asked, looking over at his brother.

"Trying to get a little more information before we start doing any kind of investigating out there." Sam explained.

"Well wake me when you figure something out. I need my four hours." Dean grumbled, turning over onto his stomach and falling asleep. Sam looked over at his brother before turning his attention back to the screen.

He was finding the same things that he had told Dean in the car. A ghost that had haunted the town for years, mainly just doing little things to annoy people. Up until the past couple weeks, when three people had lost their lives due to things associated to the ghost. One woman had fallen down some stairs, another had been impaled by the ghost throwing something, and a third man had been crushed to death by a falling bookcase. So far, no connections. They didn't live in the same house, let alone the same neighborhood. They didn't have the same last name. They weren't the same age. To Sam, there was no visible connection. And most of the time, ghosts usually had some sort of pattern.

"Guess we'll just have to talk to their families and see what we can uncover." Sam said aloud, even though he knew that Dean wasn't listening. He looked over at Dean, who really needed the sleep. He decided then that he could handle the interviews himself. He dressed himself in his FBI suit and grabbed his ID for Agent Jennings. He left a note for Dean, telling him he would call if anything major came up, and headed out to start the interviews.

He went to the boyfriend of the first girl. Her name was Zoey.

"I don't know what happened." Her boyfriend, Craig, told Sam as he set across the table from him. "We were carrying boxes. And she just slipped right in front of her parents and me. And she fell down the stairs."

"Did anything strange happen leading up this? Was there anything weird in the house?"

"I mean, it was cold. But it's winter time. I expected it to be." Craig told Sam. "Everything was great. We had went to the museum up off of 4th…"

"What museum?" Sam asked.

"Um, that one that talks about those musicians who died in the plane crash." Craig said. "Why is that important?"

"I just have to cover all the details." Sam explained, writing down the information.

The interview with the second girl's mother went the same way. And surprisingly, she had taken her niece and nephew to the museum right before she had been stabbed. And the third victim, Jackson, had also been to the museum, his brother informed Sam. Sam pulled out his phone and called Dean while heading back to the car.

"You ditched me Sam." Dean yawned when he answered.

"I left a note." Sam defended. Dean looked around and finally found the note, thinking that Sam had run off.

"I knew that." Dean said. "So, what did you find out?"

"The only connection between the three is that they visited the Museum of History." Sam explained. "Should be worth checking out."

"It's going to be a lot of classical music and Civil War stuff, isn't it?" Dean asked.

"How am I supposed to know?" Sam asked. "We can scope it out during the day time, or go do some after hours exploring."

"Where's the fun going during visiting hours?" Dean asked with a laugh. "Just get back here. Oh, and get some food on the way."

"Yeah, yeah." Sam hung up and went to go get some food from a place close to their motel. A salad for himself,with chicken and light dressing, and a burger and fries for Dean. He didn't even forget the pie this time. He even got himself a slice, because it actually looked really good. He headed back to the motel where Dean was waiting with the laptop and some beer.

"Mmm, and you even got the pie. Good job Sammy." Dean laughed. Sam rolled his eyes and set down with his salad and the smoothie he had snagged for himself, since he really wasn't in a beer mood. He took the laptop from Dean, surprised to see that he was already on the museum website.

"I can't find anything man." Dean said. "I looked it over."

"Well, sometimes the best way to get results is by doing." Sam pointed out. Dean nodded and took a sip of his beer. They researched all night, until the museum was to close. They packed up the gear they needed and headed out. It was just a local little thing. Nothing big.

"So, we go in and shoot Casper?" Dean asked.

"Or try to figure out if the ghost is even here." Sam pointed out. Shotguns full of rocksalt in hand, the boys headed to the building. The lock wasn't hard, and from the looks of it, there wasn't much in security. The building was dark, minus a few emergency lights. But the flashlights they had cut through the darkness with ease.

"This place would be cool to visit." Dean laughed.

"Yeah. It's pretty interesting." Sam said. He leaned forward to read a plaque with information when he could see his breath. "Uh, Dean?"

"What?" Dean asked. Before Sam could say anything though, an old style jukebox in the corner flickered to life and the guitar into to La Bamba started. "What the hell?" Sam turned around, his flashlight slicing through the darkness, until it came upon a third body standing there, beat to hell.

"Shit!" Sam gasped. Dean went to his side quickly and shown his light at the other person.

"Is that...is that who I think that is?" Dean asked. Sam nodded.

"That's Ritchie Valens."

PLEASE REVIEW!


	4. Chapter 4

**Warnings: None that I can think of**

 **1949**

JP Richardson drove his father's brand new Chevy truck down the dusty roads outside of Sabine Pass. It was pitch black outside and he had not passed anyone in miles. It had been two years since he had graduated high school, and all the glitz and glamour that he thought was coming his way hadn't even shown up. He was working part time at the radio station, but there was no sign that he was going any farther than that. Nothing was turning out the way he wanted it.

He had heard from a friend, who had heard from a friend, about Robert Johnson. While he didn't believe that he could actually sell his soul for talent, part of him had been itching to try it since his friend put the idea in his head. He had found a dirty old book when him and his friend had broken into the "witches land" once. It talked about selling your soul and the ingredients you needed. While he had some of them, the other he didn't know where to find.

"I know this isn't real." JP said to himself as he parked the truck on the side of the road at the crossroads. "This isn't real. Nothing is going to happen." But he still got out of the truck with his coffee can containing the items he needed.. He buried it right in the middle of the crossroads and waiting, but nothing happened. "Knew it." He turned to leave, but almost ran into a man.

"Hello JP." The man said. JP stood there, confused.

"Who are you?" He asked. "How do you know me?"

"I know a lot about you." He laughed. "As for who I am? My name is Crowley."

"Uh huh." JP said, staring at him. "What are you doing out here in the middle of nowhere?"

"Well, you tell me. You called me." He smiled, his eyes glowing red. JP gasped and stepped back. "Now, now, now. Don't tell me you're upset I'm not some pretty woman in a tight dress. I mean, I could put on a dress. It just won't be as flattering."

"I should go." JP said, turning to leave. Crowley spoke up then.

"I can get you the head position at the radio station." Crowley said. JP froze and turned to look at him. "I can make you rich. Talented. Anything you want."

"Just like Robert Johnson?" JP asked. Crowley laughed some.

"He wasn't one of my projects, but yes." He said. "All you have to do is agree."

"And what do you get from it?" JP asked.

"Sometime in the future, I will come for what I want. For now, I just want to sit back and watch you reap your rewards. That is all." Crowley said innocently. "Come on JP. It could be all that you ever wanted."

"Okay." JP said after a couple moments. "What's the worse that can happen?"

"That's the spirit." Crowley took a step towards him.

"So, how do we do this? Do I need to sign something? Shake hands?" JP asked. Crowley smirked.

"Not quite. I seal my deals in a different way." Crowley got closer to JP.

"Oh. Oh!" JP closed his eyes and pretended he was kissing Betty Hart from his math class. As soon as it was over, Crowley was gone, leaving JP standing in the middle of the crossroads. Only the crickets and the stars knew what he had done.

But the next morning, he was offered a full time position at KTRM.

 **Present**

"There's no way." Dean said. "The only celebrity ghosts we ever fight are serial killers. There's no way that this is really Ritchie Valens." The ghost in front of him flickered, like it was mad at the words Dean had just uttered.

"I think you're pissing him off." Sam warned. Dean looked at the ghost.

"Can you understand me?" Dean asked.

"Of course I can." The ghost said. "Now, the question is, can you understand me." Dean turned back to look at Sam before looking at the ghost. "And yes, I am Ritchie Valens."

"Were you the one who killed those people?" Sam asked. Ritchie turned away from the Winchester's then, closing his eyes. "Why?"

"I didn't mean to." He said.

"Yeah, they all say that. But you still killed three people." Dean pointed out. Which didn't help the situation much, because Ritchie threw a whole stack of pamphlets across the room.

"It was an accident!" Ritchie yelled. "I just want someone to help me!"

"Help? Help with what?" Sam asked.

"I've never been able to leave Clear Lake." Ritchie explained. "I know I'm dead. I know what happened to me and the other two. And I've been wanting to move on. I just want to see Donna again."

"Why can't you?" Dean asked.

"I don't know!" Ritchie was upset and the temperature had dropped in the museum. "I just want to go home!"

"Just relax." Sam said, trying to calm the upset musician. "You said you needed help."

"I tried to communicate to people. To talk to them. But it's like I'm speaking Spanish to them. Or I am talking but they can't hear what I'm saying. And I just get so angry! I never meant to hurt anyone!"

"We're going to try to help you, okay?" Dean said. He looked at Sam. "Is there anything that could be tying him here?"

"He died here, Dean." Sam said. "And you call yourself a music buff."

"Well, I am so sorry." Dean rolled his eyes. Dean looked back at Ritchie. "We're going to figure this out."

Ritchie tried to respond, but, no sound came out. Then he disappeared in a flash. Sam and Dean looked at each other. "Must have drained his batteries or something."

"Let's look around here. See if anything of his could be tying him down." Sam said. The boys split up, walking around the museum. They let their flashlights slice through the dark. Nothing seemed to jump out at them.

"Dean." Sam said a little bit later. Dean made his way over to Sam, where he had his flashlight pointed at a glass case. Dean turned to look, seeing a guitar behind the glass. "Think this could be it."

"Yeah, should be." Dean reached into the bag he had and grabbed a crowbar. He slammed into into the glass case. Sam reached in to get the guitar. Ritchie appeared then, his eyes wide. He was waving frantically, making Dean look at him. "Relax. We got this. You'll be with Donna soon." But Ritchie was still obviously upset. And that's when a crash behind Dean turned his attention back to Sam, who wasn't there.

"Sammy?" Dean asked. He saw the guitar laying on the ground, crushed to pieces from the impact with the concrete floor. Dean turned around in a circle. "Sam!"

"He got him." Ritchie finally said. "He was right here. He got him."

"Who? Who got him?" Dean asked. Ritchie flickered, obviously distraught. "Ritchie!"

"The demon who killed me." Ritchie explained. "He killed Buddy and he killed JP and me." Dean just stared at the ghost. And then he disappeared, leaving Dean with no answers.

And no brother.

Sam laid on the cold ground, groaning in pain as he came to. His head was pounding. He opened his eyes, blinking. He had expected to see Dean towering over him, worry on his face. But he didn't see his brother anywhere. In fact, there wasn't even a ceiling over him. Sam pushed himself to his feet and looked around. This sure didn't look like Iowa, or at least the part he had been in.

"What the hell?" Sam asked himself, looking around. He spied a building in the distance. There were a couple old cars sitting out in front of it, shining brightly in the sun. He could see some kids running around while their parents watched. He thought it was a car show, but why were the women that were there wearing dresses that looked like they had came straight out of Grease?

He made his way towards the building, his head spinning a little. A couple of the women that were sitting on benches watching their kids stopped their chatting when they saw him. He was a sight to be seen. Long, shaggy hair. Dusty clothes. He looked like he had just gotten off his motorcycle or something. He made his way to the building, surprised to see it was a visitors center. A water fountain was the first thing he went to, gulping down mouthfuls of water.

Once his mouth didn't feel like it had a mound of dirt in it, Sam made his way over to the visitors center. There were plenty of brochures on things to do…in Lubbock, Texas?

"What the hell?" Sam mumbled again, grabbing one of the brochures and reading it. The font and everything screamed 1950's. "Oh god, I time travelled, didn't I?" He groaned and rubbed his head. That's when the sound of a short burst from a police siren reached his ears and Sam knew he had even more trouble.

"Do you realize that this is a public park?" The cop asked, walking up to Sam. "Do you have any idea what time it is?"

"Uh, no?" Sam asked. The cop squinted at him.

"Son, just how drunk are you?" He asked. Sam was about to argue, saying he wasn't drunk, when another man came up and place a hand on his arm.

"Thank you officer. This is my cousin and he gets confused sometimes." The man said. The cop rolled his eyes.

"Yeah, sure. Just keep a better eye on him Jennings. I would hate to put him in the drunk tank." With that, the cop turned and left. He really didn't feel like doing his job today. He just wanted to relax.

"Thank god. That man is an asshole." The other man laughed.

"Thank you?" Sam said, a little unsure.

"Don't mention it. I know how it feels to drink so much that you don't know where you are." He laughed. "I'm Waylon by the way. Waylon Jennings." He offered his hand for Sam to shake it. Sam stared for a second before shaking his hand.

"Sam Winchester." Sam said. He knew that this wasn't his time. Just that feeling in his gut. So he didn't feel as worried about using his real name. Plus, it's a little hard to think of something when the man you just used for a fake ID was standing right in front of you.

"Where are you from Sam?" Waylon asked. "Judging by the hair and clothes, I would say it's not Texas." He scanned him up and down. "You're one of them beachheads from California, aren't you?"

"Guilty." Sam said. Waylon laughed.

"What brings you to Texas?" He asked. They started walking, heading towards where Waylon's car was parked. Sam didn't know why he was going with him. Every hunter instinct was telling him to hide in the shadows. But this was Waylon Jennings. He had grown up to his music playing on a radio in Bobby's kitchen while he helped him make chili.

"I'm really not sure." Sam said. "Guess I'll just be passing through." Waylon looked Sam up and down.

"You look like a drifter that has watched one too many John Wayne movies." Waylon said with a laugh. He opened up his car door and took out a flask. He took a quick swig of it. "Want some of this? Might help if you got a hangover. My brothers always said a little hair of the dog never hurt anyone." Sam took it and sipped. It tasted a little watered down. Waylon seemed satisfied though when Sam handed him the flask back. "You hold your liquor well."

"Thanks?" Sam asked. Waylon motioned to his car.

"Need a ride somewhere? I can take you into town and you can see about getting yourself something to eat."

"I…" Sam paused when he glanced in the car. Carved into a piece of the wood grain inside the car was something that Sam recognized after a second. One of the sigils of Solomon. Sam turned to look at Waylon, his eyes wide. "That flask was silver wasn't it."

"Yeah. So?" He asked.

"And there was holy water in the whiskey." Sam added. Waylon stayed silent this time. "Oh my god, you're a hunter, aren't you?"

"I mean I-I hunt deer and stuff occasionally." Waylon said. Sam shook his head.

"You know what I'm talking about." Sam told him. Waylon sighed.

"Well, I know you're not a monster." Waylon said. "So you're a hunter Sam?"

"And a member of the Men of Letters." Sam added. Waylon rolled his eyes.

"Stuck up bunch if you ask me." He said. "I met this one few years ago named Henry or something. He was down here on some sort of mission. He needed help pulling that stick out of his ass."

"Henry Winchester?" Sam asked.

"Yeah, sounds about right." Waylon motioned for Sam to get in the car.

"That's my grandfather." Sam said without thinking. Waylon froze.

"He's only in his thirties." He said. Sam was mentally kicking himself. Waylon stared at him. "Where did you say you were from again?"

"Uh…" Sam couldn't remember. Whatever had happened to him back at the museum had taken away from of his short term memory. Everything felt fuzzy. He wouldn't be surprised if he had a concussion. Sam's phone fell from his pocket then. Waylon picked it up.

"What the hell is this?" Waylon asked, flipping the device in his hand. "Is it like a CB or something?" Sam reached out to grab it, but Waylon hit the home button, lighting up the screen. "No service found...well, I'll be damned."

"What?" Sam asked.

"I've read about this. I just didn't know it was actually able to happen."

"What?" Sam asked again, more than a little confused.

"Time travel." He said. "I've read hunting journals. They talk about people ripped from their timelines, misplaced into others with no way of returning home. I just didn't know it was real until I met you." Sam was surprised that he was taking this all so well. Maybe it was just because he was off his game, or maybe he had been knocked out by whatever that was that attacked him when he grabbed Ritchie's guitar. "You're going to have to blend in while you stay here, ya know?"

"Um, yeah I kind of figured. But I doubt I'll be here for long." Sam said. "By the way, where is here?"

"Welcome to Lubbock, Texas. 1958."

"1958?" Sam asked. Waylon nodded. "God, Dean is going to love this when I get back."

"Remember what I said Sam? I've never read of anyone returning home. As far as I know, there's no way to." Sam stayed silent. "But don't you worry. I have the perfect person for you to meet. Him and his wife will help you blend in. Promise."


	5. Chapter 5

**Warnings: Spoilers, mainly if you haven't seen season 8**

Dean burst into the motel without a care in the world. He had a small piece of hope that Sam was in the motel. That maybe he just got zapped back there. But all that laid in front of him was a motel room minus his brother. Dean had checked everywhere, just in case Sam was hiding, even under the bed, but there was nothing.

"Son of a bitch." Dean hissed behind clenched teeth. He wanted to hit something. Sam said this was going to be a nice hunt to get their mind off of things. But all Dean had to show for it was a ghost of a dead musician who couldn't move on and no brother. Dean tossed his bag onto his bed and headed for Sam's laptop that set on the yellowed table in the corner. He opened the screen to turn it on.

But nothing happened.

"Oh come on." Dean growled. He made sure it was plugged in and the battery was okay before trying it again. He heard it warming up, the fan running.

Then it died again.

"You have got to be kidding me." Dean took deep, calming breaths. Why was this happening now? He just wanted to research more about Ritchie and the others. Maybe he could find out something that he could use to break the poor kid's curse, and maybe that would bring Sam back from wherever he was. But with the Winchester luck, when it rained, it poured.

Dean tried for a little while, trying to fix the computer to the best of his ability. Had Sam been complaining about it recently? With all this trial crap going on, Dean had been focusing more on Sam's health and not what Sam was saying. He had been focusing more on Kevin and trying to get those tablets translated before Crowley got his meat hooks in him.

He probably would've ended up throwing that damn laptop across the room if his stomach hadn't told him to fuel up before doing anything rash. Dean sighed, knowing that it had been awhile since he had eaten and he knew what starvation could do to your brain.

Thankfully, on his way over to the little diner a couple streets over, he saw a library, unfortunately, they didn't open for another hour or so.

That time was spent waiting for the waitress who was flirting with another girl sitting at counter. Once she realized Dean was there, she reluctantly took his order. It seemed to take forever for her to realize that his food was sitting on the rack to be delivered. And he forced himself to not just inhale the food. But once he was done, he headed to the library. He had never been so glad to see an open sign before.

The sweet librarian at the desk, playing solitaire on the computer, smiled at Dean when he came in. And she showed him to the archived newspapers when he asked, calling him sonny and hun the whole time. Dean set down with the newspapers and started looking through them. He had remembered seeing the headline before, a long time ago on some video on Youtube or something like that. Four killed in the plane crash. The three musicians and the pilot. He just wanted to see if there was something hidden in the story that he missed.

But when he found the newspaper he wanted, something didn't seem right.

Five killed in plane crash.

"I don't have time for this Mandela Effect crap." Dean groaned. He started to read through the headline story, but something made him freeze and go back up. The five pictures.

Buddy Holly; musician.

Ritchie Valens; musician.

JP "The Big Bopper" Richardson; musician.

Roger Peterson; pilot.

Sam Winchester; road crew.

A picture of Sam, standing with another man, was there in clear black and white for Dean to see. The caption said Winchester (left) and Waylon Jennings (right), right before the plane crash.

What the hell was going on?

But it wasn't just the New York Times that said those five names. All of the ones that were right there had the same names listed among the dead. Dean couldn't feel anything. All he could do was just stare at the newspaper.

Sam was going to die in that plane crash and he didn't know how to save him.

"I know where he is then." Dean said, standing up. The nice librarian let him use a computer. He had access to everything that he needed. The shock of finding out that, not only had Sam been sent to the past, but he was dead, was fueling Dean's researching. He had to find out everything. That was the only way he was going to be able to save Sam.

He read through articles, looked at pictures. According to his research, Sam had joined Buddy Holly's band in November of 1958. Right before the Winter Dance Party Tour. Eyewitness accounts said that they didn't see Sam get on the plane with the three other musicians. Waylon Jennings was supposed to be on the plane, but he gave it up to the Big Bopper since he had the flu and needed to rest. Ritchie Valens had won a coin toss to get on the flight.

According to the limited biography about Sam that he found, Waylon took custody of his body after his death and buried him in the Jennings family plot. Well, according to some accounts. Others say that the musician had him cremated, claiming that was what Sam wanted. So Dean wasn't sure what to believe. But one thing he did know was he had a time machine with wings within calling distance.

"Cas." Dean said into his phone as he left the library with copies of everything he could fine, as well as some instructions on how to possibly fix Sam's laptop. "Cas, come on, I need your help. Call me or get your feathery ass over here. Now."

"Dean's calling for me." Cas said as he set in the chair across from Naomi. "I need to go help him."

"Ignore it Castiel." Naomi warned. "We have more important matters to worry about right now.

"But…" Cas started to argue, but Naomi glared him down.

"Ignore. Him." She hissed. Cas nodded and closed his eyes, blocking out the worried voice in his head. "Good." She smiled and reached for something in her desk. "Just relax Castiel. We have a lot of things to discuss." She grabbed out her drill and made her way to the angel.


	6. Chapter 6

**Warnings: None I can think of**

 **1958**

Waylon and Sam pulled onto a quiet, suburban street about ten minutes after leaving the park. Sam watched all the clean houses with the manicured lawns. He made a note to himself to make his way back over here when he got back to his own time to see how well time had treated everything. Waylon pulled into a driveway by another car. Sam could hear the sound of guitar then. He looked forward and gasped.

Sitting in a chair, strumming a guitar, was none other than THE Buddy Holly.

"Is that who I think that is?" Sam asked himself, but Waylon heard and smiled.

"Trust me, he's pretty down to earth." Waylon patted Sam's arm before getting out of the car. Sam followed, standing awkwardly behind Waylon.

"Sounds good man." Waylon said, clapping his hands when Buddy had finished the rift he was working on. "Something for that upcoming tour?"

"Not sure yet." Buddy looked around Waylon. Sam was standing there, looking completely out of place. "Friend of yours?"

"Oh yeah, this is Sam. We go way back." Waylon said with a smile. "He's new around these parts and I thought maybe you and Maria could help him out some. Get him blending in." Buddy stood up and walked to Sam.

"Do you play guitar?" He asked.

"Uh, a couple chords." Sam said with a shrug. Buddy looked him up and down.

"I think I have the perfect job for you." He smiled and offered his hand. Sam shook it, feeling that this was a test. John had always taught the boys that you could tell a lot about a man by his handshake. He had no doubt that's what Buddy was doing right then. "Some of the members of the road crew quit a while ago. How'd you like that job?"

"Yes, sir." Sam said. Buddy laughed.

"Please, let's drop the formalities. I'm twenty-two, not forty." He laughed. "Come on, I'll introduce you to Maria. Do you have a place to stay?"

"No." Sam said.

"Well, we have an extra room." Sam looked back at Waylon, who just smiled at him. Sam followed Buddy inside the house. They walked into the kitchen where a young woman was standing at the counter. "Sweetheart?"

"Hey honey." She smiled and pecked his lips before turning to look at Sam and Waylon. "Oh dear, I didn't know we had company. I must look a mess."

"Ah, Maria, you know you always look good." Waylon laughed. She just blushed and smiled before turning her attention to Sam.

"This is Sam. He's joining my crew." Buddy explained. "And he's going to be staying with us until he can get on his feet or decides to head back home to...where are you from again Sam?"

"Uh, California…" Sam said, glancing over at Waylon. The musician nodded. Maria eyed Sam a little, but didn't say anything.

"Well, welcome to our home Sam." Maria said with a smile. "Do you have any bags or anything? Extra clothes?" Sam shook his head.

"I lost them along the way." He told her. "I lost everything."

"I'm not sure if anything of mine would fit you, but there is a big and tall shop on main that would have stuff that would fit you. Because I doubt you want to wear the same clothes over and over again." Buddy laughed.

"I'll go pick up a few things." Waylon said. "Why don't you stay here and get situated. Maria and Buddy are nice, I promise." Sam smiled.

"Thank you." He said. Waylon left and Buddy went back out the the garage, leaving Maria and Sam alone in the kitchen. There was an awkward silence between the two of them, before Maria finally spoke up.

"You're not from California, are you?" She asked.

"Uh, yeah." Sam said. Maria shook her head.

"Come with me." She said, motioning for Sam to follow her. "I know you're not from California and I know that you're not from this time." She went to the linen closet in the hallway and dug around in it before pulling out a box. "My husband thinks this is things from Puerto Rico." She handed the box to Sam. "Go on, open it."

Sam carefully set the box down and took the lip off. Inside was a folded up pair of blue jeans, a Guess t-shirt, a pair of Converse, a flip cell phone with the old Sprint logo on it, and an ID for one Maria Santiago.

Born in 1968.

"See." Maria said. "Now, I remember going with my friends to a concert. There was this man there. He kinda looked like Buddy. He was charming and suave. I remember heading to his car with him, then I woke up here. That was four years ago." Sam just kept staring at her, completely in shock. First, he found out Waylon Jennings was a hunter, and now Maria Santiago-Holly was a time traveler who was stranded…

"I came here from 1990." She explained when Sam made no move to say anything. "You look like someone who listened to Nirvana and Pearl Jam. Are you from the 90's too?"

"Uh, more like 2013." Sam said. Maria's eyes widened.

"2013? What's it like?" Her eyes were so full of wonder. Sam was about to say something when Buddy came in, guitar in hand. Maria took the box and put it back in the closet. The less he knew, the better.

"Is Maria showing you around?" He asked.

"I was about to honey." She smiled at him. "I just wanted to get to know him a little more. California sounds amazing." She winked at Sam, sealing the secret between the two displaced people.

God, he was going to have so many stories to tell Dean when he got home.

Sam slept amazing that night. It wasn't the bunker, but the Holly's home was actually quite cozy. Waylon had promised to stop by to make sure that was settling in well. He knew that Maria would help Sam adjust. And she was. Because currently, Sam was sitting on the floor in front of her couch wearing black pants and a white shirt while she greased back his hair.

"Buddy won't let me grease his hair." Maria laughed as she combed back Sam's long locks. Buddy came in then and settled himself down on the big, comfy armchair.

"That's because it is ridiculous." Buddy laughed. Sam looked up at him. "But it looks good on you!"

"Oh Charles, stop it." Maria said. Sam glanced over at the musician.

"Charles?" Sam asked. Buddy sighed.

"Buddy is a childhood nickname," He explained. "Plus, do you think I would have this much success if I used the name Charles Holly?" Sam just smiled. "Waylon might be able to get away with it, but I don't think I could use my real name."

"Yeah, I guess you're right." Sam replied.

"So, I thought that you could go with me today to set up for practice." Buddy told Sam.

"Uh sure. Do you think I'd fit in?" He asked. Maria laughed.

"Better than that surfer hair of yours Sammy." She said. Sam felt a little pang in his heart. Sammy. God, he was really missing Dean.

"Well, if you say so." Sam said quietly. Buddy smiled and went out to get things ready. Sam set on the floor in front of Maria in silence.

"Are you okay Sam?" Maria asked, finishing up his hair.

"Yeah." Sam responded, but Maria could tell his heart wasn't in it.

"You know, I left behind a little sister and a dog in the 90's." Maria told Sam. "My sister was thirteen. She begged me to take her to the concert with my friends and I told her no. The last thing I ever said to her was 'I wouldn't be caught dead hanging out with my baby sister'. Now all I want to do is see her again."

"We'll get out of here." Sam said. Maria shook her head. "What? Why?"

"I'm in love Sam." She said. "I love him."

"But you know what happens to him." Maria nodded. "Don't you want to avoid that heartbreak?"

"Some things are just worth it." She said. "Talk to me again in March and see if I still want to stay." Sam turned to look at her. "It's like that new Garth Brooks song. I could have missed the pain, but I'd have to miss the dance." She patted Sam's shoulder. "Well, you're ready to go Sam."

"Thanks Maria." He got up and grabbed the leather jacket that Waylon had got him. If Dean could see him right now…


	7. Chapter 7

**Warnings: It will probably get a little emotional**

 **Present**

Cas wasn't answering. The one time that Dean needed him to show up and he wouldn't even answer him. Dean wanted to punch something, mainly Cas, but he needed to keep his cool. The roles had been revered on them just a year ago, when he met with Eliot Ness. Of course though, Sam hadn't found out that his brother was dead through a newspaper article.

Dean had no leads except for a ghost with random bouts of silence.

He walked back into the motel room. Part of him secretly kept hoping that Sam would just show up. But that would make things easy and the universe wasn't really known for giving the Winchester's a break. Dean threw all his stuff down on the table and went to get a beer from the fridge. He glanced over at the laptop, seeing it on and working just fine.

"I freakin' hate you." He grumbled at the piece of technology before sipping his beer. He set down in front of the offending object before starting in on more research. He had tried to get Cas's attention, but still no answer. He shouldn't be surprised though. Cas always seemed to disappear when Dean or Sam needed him the most.

But at least now he could learn about everything from the comfort of a motel room. And boy, was Wikipedia his best friend. He knew that it wasn't always the most reliable source, but it was a lot easier to read than other sites were.

But after an hour or so of searching, all he had to show for it was what he had seen in the newspaper back at the library. He leaned back in his chair, ready to give up. But that's when he spotted a link on his web browser.

Holly Widow to visit Clear Lake.

"Son of a bitch." Dean grumbled. He looked at the time and place. Today at the Fieldstone Park, in one of the insulated buildings. There was some sort of dedication or luncheon or something. Dean didn't really care. But if she was here, and she was alive back then, then maybe she could give him some answers about Sam. He jumped back up and grabbed his jacket. He didn't care if he was tired or anything like that. Sam was on the only thing on his mind, and if this woman had some answers, then he was going to be there.

Maria Santiago-Holly set at a table while everyone chatted around her. She was ready to go back home. She felt so alone anymore. Everyone that she talked to back then was gone. Buddy. Waylon. Sam. God she missed them. She had kept in touch with Waylon for awhile, since he knew what she was going through. But he became a big star and had to keep his hunters life separate from the spotlight. Then he died in 2002 and anyone who knew her secret was gone. Buddy never knew, and Maria was sure he would have laughed if she had told him. But then again, maybe not. He did propose to her on their first date.

She seemed lost in her own world when a young man approached her table. He looked down at his phone then up at her, like he was making sure it was the right person. He approached her, having some bad experience with older woman before. He just hoped she wasn't the type that "Slept with her peepers open".

"Ms. Holly?" Dean asked. Maria looked up at him, her eyes widening ever so slightly. "You don't know me, but my name is Dean…"

"Winchester." She said.

"How did you…"

"You look just like your picture." Maria said, cutting Dean off. She saw the look on his face. "I think you and I need to talk." She stood up slowly, her stiff joints protesting the whole way. She took her cane that was leaning against the table. "I need some air." She said in case anyone around her table was listening. She started to head to the door, waving for Dean to follow her.

It was chilly outside as Maria and Dean walked out of the warm building. She looked up at the grey sky, like she was expecting something. Dean stood there awkwardly. What did she want to say to him out here that she could say in there.

"Buddy adored your brother." She told him before walking along. It wasn't hard for Dean to keep up with her. "A lot of people did. Myself included."

"That doesn't surprise me." Dean told her. She smiled.

"Sam and I had a lot in common. It was nice finally having someone to talk to that could understand what I was going through." She led him to a gazebo and set down on one of the benches. Dean set down beside her.

"What do you mean?" Dean asked. Maria smiled fondly, remembering.

"You must know that your brother disappeared, or you wouldn't be asking about him." She said. "And you must know where he ended up, or you wouldn't be here talking to me. Unless you were just a big fan of my husband." Dean did the math then. Her and Sam had a lot in common. Dean knew that Sam had been sent back in time…

"You're a time traveler?" Dean asked.

"I guess that's what you can call it." Maria said. "More like I was taken from my time and forced into a new one. I was twenty-two went I was taken." Dean set there for a second, taking it all in. She could be tricking him, but he seriously doubted it. He wasn't getting any evil vibes off of her.

"Okay, so there's something out there sending people back to the 50's?" Dean asked.

"It's a demon." Maria said, matter of factly. Dean just stared at her. "I'm assuming if Sam knows about that kind of stuff, you do too." Dean just blinked. How was he supposed to react to this? A woman he had only met five minutes ago knew his brother, claimed to be a time traveller that was snagged by a demon, and knew that he was a hunter. What the hell was going on?

"I need you to tell me everything." Dean said.

"What do you mean?" Maria asked.

"I need any details that you can give me so I can get my brother back." Dean told her. Maria just shook her head. "What?"

"You can't get him back." She told him. "I tried for years to get back to my time, and the only way I did was by growing old. And Sam got on that plane with Buddy, Ritchie, and JP." He could see the tears coming. "I watched as Buddy taught him to use the drum kit, and Sam took good care of the instruments for him…"

"You don't understand," Dean said, staring Maria down. "I am getting my brother back. There's no can't or anything like that. Sam is coming home." Maria nodded, looking down at her hands. She wished that he little sister had cared as much about her as Dean did Sam. But as far as she knew, her sister probably hated her. She didn't realize she was crying then until Dean placed a hand on her shoulder. "Are you okay?"

"Y-yeah." She whispered. But Dean could tell she was lying.

"Yeah, sure." He laughed some. "You're as bad as Sam about hiding your emotions. Now spill."

"I just...I knew what was going to happen to him and I didn't stop it." She confessed. Dean knew then that she wasn't talking about Sam. She was talking about her husband. "I knew he was going to die and I did nothing! I let him go. I let him and Ritchie and JP get on that plane and...and…" She covered her face.

"You did what you had to do." Dean said. "If you had stopped him, you might have changed history for the worst."

"Don't you think pulling Sam from the past will hurt things then?" Maria asked. Dean shook his head no. "Why?"

"Because I know he's not supposed to be there. And I'm going to bring him back." Dean had to smile. He was doing what he was supposed to be doing. Protecting Sam. "Now, you said it was a demon?"

"Yes." Maria wiped her eyes. "He came to see me and he left the smell of sulfur. And Waylon knew what it was. He said that the smell was all over the crash site too. And when he buried Sam, he said it was on his clothes. Waylon knew what he was talking about."

"Okay so this Waylon guy said it was a demon and you believe him?" Dean asked.

"I did some research on my own." Maria said. "I might have been used to computers starting to enter society, but I still knew how to read journals and books. Waylon and I figured it out with all the clues that we both had. The sulfur, the black eyes…"

"Okay, well that makes more sense then." Dean said. "You probably should have added the black eyes."

"I didn't think of it." She rested a hand on her stomach, thinking back. "He came to see me, wearing a face that looked slightly like Buddy. He said he was an interviewer, but then he looked at my stomach and his eyes flashed black for a moment. I found out after Buddy and Sam died that he knew I was pregnant."

"The demon killed your baby?" Dean asked. He knew demons were cruel, but killing an unborn baby of a woman who just lost her husband?

"Technically." Maria said. "I'm a firm believer that he caused the plane to crash. And that killed Buddy. I found out he had died while listening to the radio and it caused me to have a miscarriage. So, in turn, the demon killed my baby." Dean stood up.

"I'm going to fix this, I promise." He looked around at the cold and lonely park. "Do you happen to know a name or anything?"

"Uh, I can't remember." Maria sighed. "I'm sorry."

"You've helped quite a bit." Dean said. He knelt in front of her and took her hands. "I will fix this Maria. I might not be able to bring your husband back, but I can kill the demon that took him and your baby away from you." Maria nodded and wiped her eyes. Dean stood up and left, ready to get to work. Maria set there for a minute before she heard someone calling for her. She hoped that Dean was right about everything.

The doors to the museum unlocked and swung open. A man not much older than Sam walked in, looking around. He had gotten a call about a possible breakin the night before, but he had denied having the police investigate. Instead, he decided to look into it himself. And sure enough, that guitar laid on the ground, just the way he figured it would be.

"Oh, what have you been up to you naughty boy?" The man asked. He looked around. "Ritchie, I'm talking to you." The jukebox kicked on then, the haunting opening guitar chords of Duane Eddy's "Rebel Rouser" filling the empty building. "Ritchie…"

"Go away Corson." Ritchie growled as he materialized. "Leave me alone."

"You don't make the rules here kid." Corson said, his eyes flashing black. "Who was here last night? I know it wasn't any of your friends, because all your friends are dead."

"Shut up." Ritchie hissed. Corson laughed.

"I think I hit a nerve." Corson said. He sniffed the air. "This place reeks of Winchesters." He closed his eyes, like he was focusing. "Ah yes. I see what happened." He laughed.

"Leave them alone." Ritchie said. Corson shook his head.

"They played with my toys. I don't like that." He pulled out his phone and scrolled through some news articles. "Ah. Little Sam. He paid the price for their meddling." Ritchie looked away.

"They will beat you." He said. Corson had a big smile on his face.

"I'd love to see them try." He said. He put his phone away and picked up the discarded guitar. He dusted it off. "One of them is already getting what he deserves. The other one will get it next." He looked back over at Ritchie. "I think you can go hide now." With that, he snapped his fingers, making Ritchie disappear. Corson took to sweeping up the broken glass, planning on what to do when he met the eldest Winchester.


	8. Chapter 8

**Warnings: None that I can really think of**

 **AN: You might want to watch this video. It'll make sense later: watch?v=AQXVHITd1N4 &t=1s**

 **1958**

November turned to December and Sam was starting to lose hope of ever getting back to his own time. The 50's weren't so bad if you could look past all the racism, sexism, wealth gap, homophobia, and everything else. It had a cool aesthetic though. Maria seemed to love being able to grease Sam's hair back to help him fit in. She really liked spending time with Sam. But Buddy did too. He was trying to teach Sam how to play drums and he was teaching Sam how to take care of the guitars and equipment for when they went on tour in January.

The doomed tour, and Sam would be there to watch it all crash down.

Buddy and Waylon were out, talking with the other members of Buddy's new band. Sam had been there when he told the Crickets "screw you" and left them behind. So he had convinced Waylon to join him and a couple others on the tour. There was this pretty cool cat from California that was going to be joining them, as well as another fellow Texas boy. Sam and Maria knew exactly who they were and what was going to be happening to them.

So Sam and Maria stayed behind while Buddy and Waylon did their thing. Sam wasn't sure what to do, so he took to helping Maria with the cooking. There was a small radio plugged in, sitting on the counter. Maria was reading through a cookbook, trying to figure out which recipe would be best for dinner that night. Sam set at the table, reading the week befores copy of Life. Elvis had just played a little bit ago, followed by one of Buddy's songs. After a few ads and some talking from the DJ, a Connie Francis song came on and Maria couldn't stop smiling. She turned to look at Sam.

"Stupid cupid you're a real mean guy." She sang. Sam glanced up at her. "I'd like to clip your wings so you can't fly!" She walked over to him, making him look up at her. "I am in love and it's a crying shame…" She leaned in to kiss him then, but Sam gently pushed her away.

"Maria…" Sam said. The song was still playing in the background and Maria stood there awkwardly.

"I just thought…" She started to say.

"You're married to Buddy." Sam told her.

"Yeah, and I love him, but you know what happens." She said.

"And I care too much about him to hurt him like that." Sam said. "You're the one that said you would have rather loved and been in pain than never have loved at all." Maria nodded and set down, hiding her face. "Maria…"

"I'm sorry. I just don't know what to do." She looked up at Sam. "What am I supposed to do?" Sam leaned forward.

"You spend as much time with him as you can." Sam said. "You love him like you're gonna lose him." Maria nodded. "I know how hard this is, but it will be okay." She smiled a little, trying to hold back the tears. "Why don't we change the subject and forget about what just happened?"

"When are you going to cut your hair?" Maria asked with a laugh. Sam glared some.

"Never." He stated, matter of factly. Maria laughed.

"Good thing the 60's is coming up. Though you might get mistaken for a member of the Manson family or something." She stood up and went back to the cookbook. "Sam, would you chop some veggies for me?" Sam went right to it, so thankful that they had moved away from what had just happened.

They spent the rest of the afternoon cooking and making small talk. Sam ignored the looks that Maria tossed his way when she thought he wasn't looking. She knew it had been a mistake to try to kiss him. She tried to just focus on the task at hand, getting ready to put the chicken and veggies in the oven. She put it in then went to do the dishes, but Sam had already gotten to them. Maria started throwing away the packaging when a song came on.

 _Day-o, day-o._

Maria stopped what she was doing and looked over at Sam, who looked right back at her with a smile on his face.

 _Daylight come and me wan' go home._

Maria started miming along with the song.

 _Day, me say day, me say day, me say day_

 _Me say day, me say day-o_

 _Daylight come and me wan' go home_

Sam and Maria faced each other and slowly started to stand up straighter, moving their arms as the song continued, smiles on their faces.

 _Work all night on a drink of rum_

 _Daylight come and me wan' go home_

 _Stack banana 'til de mornin' come_

 _Daylight come and me wan' go home_

Sam and Maria started mirroring each others movements, touching their head with one hand and their side with the other, switching back and forth between head and side. Sam reached over and grabbed an empty stockpot and flipped it over to use it as a drum while Maria kept dancing.

 _Lift six foot, seven foot, eight foot bunch_

 _Daylight come and me wan' go home_

 _Six foot, seven foot, eight foot bunch_

 _Daylight come and me wan' go home_

Sam put the pot down as they stacked their hands, making it look like they were building a tall tower. The song kept playing and they kept dancing until they heard the garage door open, meaning Buddy was home. Maria turned down the music and went to check on her chicken. For a moment there, they both forgot about their situation, living in the moments that laid several decades ahead of them. A movie that Sam watched with Dean at a theater in some little town, and a movie that Maria went with her friends to see because Michael Keaton was just so dreamy.

"Smells good in here." Buddy said, hanging up his jacket and kissing Maria. "What were you two up to today?"

"Just cooking and listening to the radio." Sam said. Maria nodded.

"I was listening to see if I heard songs by either of those boys you'll be touring with next month." She cringed a little. The pain weighed heavy on her heart, knowing that in a little more than a month, her husband would be long gone.

"Well, Sam and I have some practice to do tomorrow. He's getting really good with drumming." Buddy patted his shoulder. "You might have your own band someday. Or you, me, and Waylon can team up and be bigger than Elvis." Sam just smiled and glanced over at Maria. They both wanted to save him,but they knew that they couldn't. Maria turned to busy herself with dinner. "Maybe I could convince you to become a singer while we're at it."

"That's more of my brother's speed, not mine." Sam laughed. He had mentioned his brother a couple times, but he played it off as he was in the military and not around much. Which was partially true in Sam's eyes, so he wasn't lying completely.

"Well, you've proven yourself to pretty good on the drums, and you're picking up guitar pretty quick. So you could probably sing like an angel but think you sound like a walrus." He laughed. Maria got toast ready for their meal. Roasted chicken with vegetables and toast was one of her favorite comfort foods from her childhood. And today, she was really missing her home and her parents. Hell, she was even missing her little sister. And even though Buddy and Sam were there, chatting away to each other, she felt like she was alone.

"How are you honey?" Buddy asked her then, snapping her out of her moment of loneliness.

"Oh, I'm great." She said, pasting a smile on her face. "I can't wait to see you two play together." She looked over at Sam, trying to hold back the tears. Part of her wanted to leave Buddy, to get away from the pain and possibly get back home. But she had been in love with him since the day she met him. She had even had a bit of a crush on him back in high school when she learned about him in her music appreciation class.

"Well, let's eat up and then maybe Sam and I can put on a show for you." He laughed. "I could call Waylon up and have him play with us too." It was nice having Waylon around sometimes, since Maria and Sam could talk openly about things to him. Sometimes Sam forgot that there have been hunters as long as there had been people, because monsters would never go away and people were always going to need saving.

Maria served the food, just like she always did, even if sometimes Sam would cook instead. Occasionally, they would get something from town, or Maria and Buddy would go out together and Sam would go hang out with Waylon or just fend for himself. Something that he was used to doing. But they had really become a family since Sam fell into this time and part of him didn't want to leave it.

But Dean was waiting for him.

The food was eaten, dishes were cleaned, and later that evening found Sam and Buddy in the garage with Maria sitting on a crate, watching them play. Sam wasn't the best drummer in the whole world, and wouldn't be winning any Grammy's anytime soon, but he kept pace for _Peggy Sue_ pretty well and even did decent on _That'll Be the Day._

"I think Mr. Winchester was lying to us about being able to play." Buddy teased. "I might just have to add him to the band." He patted Sam on the shoulder. "Holly and Winchester could be a good band name." Sam just had to nod. He knew it would never happen unless he decided to intervene and save Buddy from getting on the plane. But he also knew how just unsinking the Titanic could change everything, down to the smallest details. And he wasn't going to be responsible for any of that.


	9. Chapter 9

**Warnings: None that I can think of**

 **Present**

It was a demon. A demon had sent Sam back in time somehow. Dean didn't even know that demons had that kind of power. Unless it was a very old and very pissed off demon, and Dean knew the perfect one for that. Well, he knew several, but most, if not all of them were dead. Except for one.

Crowley.

He was sure that the self proclaimed King of Hell would be petty enough to hold on to the spirit of a teenage boy who was a victim of circumstance. The only thing he didn't know was why he would do that. There was more to the story than he knew and he needed to get to the bottom of it. And he needed Cas to answer his freakin' calls already!

There were all kinds of things that Dean was looking into. Could Ritchie have made a demon deal? Could he have pissed off the wrong demon? Wrong place at wrong time? Considering that Ritchie was only 17 when he died, Dean found it hard to believe that the demon deal was the right path, considering that most of them were 10 year deals and Crowley wasn't that much of a heartless bastard.

"God, where is Sam when I need him?" Dean asked, looking over at the chair Sam would have been sitting in. It's not that Dean minded doing the research, it's just Sam loved doing it and he would much rather Sam be there.

"Dean." A voice said behind him. Dean jumped up, ready to shoot, when he saw Cas standing there.

"Son of a bitch." He growled, laying his gun on the table. "Where the hell have you been?"

"I've been busy." Cas explained. Dean rolled his eyes.

"Yeah well I think we've got things that are a little more important right now." Dean said. Cas looked around the room.

"Where's Sam?" He asked. Dean laughed.

"Sam is in the 1950's because of a demon that is holding a ghost hostage." Dean explained, making Cas look at him like he was crazy. "And I've been calling you so you could go back there and get him, because he's going to die in a plane crash."

"How do you know that?" Cas asked. Dean turned the laptop around to show the news article, listening Sam as one of the dead. "Oh."

"Oh? That's all you have to say?" Dean asked. "Go back there and get him!" Cas closed his eyes, trying to hone in on Sam's soul so he could pull him out, but everytime he thought he got close, he was pushed away. "Why are you still here?"

"I can't get to him." Cas said.

"Can't? Or won't?" Dean asked.

"I can't." Cas said again. "I'm trying, but it's like something is blocking me from getting to him."

"How can something be blocking you?" Dean asked. Cas just shrugged. "Oh for the love of god…"

"You said it was a demon, right?" Cas asked. Dean nodded. "Well, maybe that's what's blocking me."

"Can you sense if it's Crowley?" Dean asked. Cas closed his eyes and tried to focus. But he wasn't getting any readings on Crowley. He could get snippets of a demon lurking around, but he couldn't find him. And it sure wasn't Crowley. Crowley loved to show off.

"It's not him." Cas said. "Whoever it is, they're old. And powerful." Dean nodded, ready to just get sent back to the 1950's when there was a knock on the door. Dean slowly made his way over, gun at the ready. Cas had his blade if he needed it. Dean slowly opened the door and relaxed, opening the door.

"Dean." Maria said, standing there. "You'd be a hard man to track down if Sam hadn't told me where you'd be." Cas stared at her as she walked in. Maria looked over at him. "Sam didn't talk about him though."

"He's a friend of ours. His name is Cas." Maria nodded.

"He might have mentioned the name once or twice. I think I heard it...when he was...praying?" She shook her head. "Anyway, I've been carrying this around with me since 1959, and now that I've finally found you, I thought it was time to give it to you." She handed Dean a worn out, yellowed envelope. Dean saw his name scrawled on the front in Sam's all too familiar handwriting.

"You've had this since 1959?" He asked, looking up at her. She nodded.

"I'm glad that living in 2013 didn't dull his letter writing skills any." She joked. "Well, I guess I should be going now."

"Thank you Maria." Dean said. Maria nodded and turned to leave. Cas closed the door behind her then looked at Dean, who was already sitting on the bed, just staring at the envelope. He slowly opened it, seeing a letter and a couple photographs inside. There was one of Sam standing with Buddy, The Big Bopper, Ritchie, and a few other people he didn't really recognize. He flipped it over and saw all the names listed, including Waylon Jennings, which surprised Dean a little. The other pictures, two of them, were almost the same, just different people. Dean laid them to the side and started to read the letter.

 _Dean,_

 _If you're reading this, I probably didn't make it back. I gave this letter to Maria Holly. Hopefully you'll get it at a decent time. And if you got this, I'm sure that you got some of the details from Maria. I tried to get back, but nothing worked. I would love to be able to come home. I'd love to be able to save Buddy and all of them, but I know I can't do that. Ritchie is actually a really nice kid in real life. I wish you could've met him before he was a ghost. I think you would love all of them._

 _I work for Buddy, so I'll be going on tour with him. Which means I will be there first hand to see him die. After it happens, I'm going to go back to hunting with Waylon. He's very old school, but he's cool. And he knows what he's talking about. Maybe I can teach him about some of the new things that we face around our time._

 _I wish I knew what sent me back. Maybe you're having more luck than me. I've tried calling to Cas, hoping that some version of him would hear me, but no luck. So I guess I'm going to get to live through the 60's and 70's. Maybe I'll hit up all those concerts that you would love to go to and buy you some shirts. Somehow get them to Bobby or something._

 _I'll see you around._

 _Sammy_

Dean looked up at Cas. Cas could see the determination and heartbreak in Dean's eyes. The letter wasn't long, but it was enough.

"Find out what it blocking you so I can shoot it." He growled. "Sammy's coming home. I'm not letting him die. Not again."

 **1959**

Christmas came and went, and Buddy and Maria treated Sam to a wonderful holiday. Buddy's family was so welcoming of him too, having heard lots of good things about him from their son over his stay there. It had felt like years since him and Dean had set down and shared a Christmas together. Honestly, it was probably before Dean went to hell. But January came quickly and Sam knew Buddy's time was drawing to an end.

"Come on Sam. We're going to be late." Buddy said as he waited for Sam. They were meeting up with Waylon at the little studio just outside of Lubbock.

"I'm coming, I'm coming!" Sam called out to him, rushing down the stairs as he slipped his leather jacket on. "This hair stuff is more trouble than it is worth."

"You know, I have a friend who is a barber…" Buddy suggested, a smile spreading on his face. Sam glared at him.

"I am not cutting my hair." He said. Buddy just laughed. He loved teasing Sam about his hair. "I thought you said we were going to be late." Buddy opened the door and motioned for Sam to follow him out to the car. The drive to the studio wasn't that long and Buddy really just liked to give Sam a hard time.

Sam had learned to play the drums on a few songs, allowing for Carl Bunch to have a few moments to relax. Buddy was making plans to start a band with Sam and Waylon once this dumb tour was over. The Winter Dance Party tour. They would be on the road less than a month but would have 24 shows. Sam wasn't looking forward to it, and honestly, neither was Buddy. He knew he needed to perform to get money, but something about this tour just seemed off to him. He could tell Maria didn't want him to go. It was the first time they would be apart for a long time since they had gotten married. He was sure that was it.

The studio had a full parking lot of cars. Sam spied Waylon standing outside of his, smoking. He tossed the butt down and crushed it with his foot when he saw Sam and Buddy pulling in. Buddy parked the car and Sam got out, stretching some as he did. He was used to going long miles in the Impala, because it was like home to him. Buddy's car wasn't bad, and it was one of the newer models for the time, but it wasn't Baby. And it killed his back.

"You guys ready?" Waylon asked, joining the pair as they headed toward the studio. "There's a lot of energy in here."

"We're going to have to meet them sometime." Buddy said, opening the main front doors. "It's either now or right when start the tour and are having to share a bus with them." Sam, Buddy, and Waylon made their way inside. Making their way down the hall, they made their way to the room where their party was waiting for them.

"Well, there you are!" Tommy Allsup saisd, standing from his chair. "Always late."

"Yeah, but I know how to make an entrance." Buddy smirked. Tommy and Carl had already met Sam and of course they knew Waylon. Carl was helping Buddy teach Sam some beats, while Tommy pouted that he was upset he didn't have a backup guitarist.

"It's nice to meet you finally." A man said, coming forward to shake his hand. "I'm JP Richardson, but everyone calls me the Big Bopper." Sam stared with wide eyes as the two musicians shook hands. Another man, one that Sam knew from his own time, came over. He wasn't as ghostly looking this time though.

"I'm Ritchie." He said, shaking Buddy's hand just like JP had. All three of these musicians together was a little surreal. Especially because Sam knew that in about a month, those three would be dead. Sam wanted to save them. He wanted to convince them all to stay on the bus, to not go anywhere near the plane that day. But he knew the consequences of his actions. Maria knew it too. That's why she had been acting so weird since January hit. It was just a waiting game now.

"Sam." Waylon said, elbowing the hunter in the side. "You spaced out on me. Are you okay?"

"Yeah, just a big of a headache." Sam smiled at him. "Was someone talking to me?"

"That'd be me." JP laughed. A hearty, deep laugh. "Are you going on tour with us? Carl here has been telling us how good of a drummer you are."

"I'm not that good." Sam chuckled, a blush started to appear on his checks.

"Sammy here is just modest." Buddy laughed. "He's actually pretty good. A few more years of practice and he might be one of the greats. I can't believe how fast he picked it up."

"My mama said it was no time before I was just learning instruments. I would pick one up and 'bam!', I could master it in about a month." Ritchie explained.

"How old are you kid?" JP asked, looking Ritchie up and down.

"Seventeen man. The sweet age, as my brother says." Ritchie explained.

"Dear god, you guys just keep getting younger and younger." He joked.

"I'm twenty-nine, if that makes you feel any better." Sam told him. JP smiled.

"Actually, yes it does." JP smirked. "AT least I'm not the oldest in the room." Sam just shook his head. "Well, I was under the impression that we were going to play for each other and not just make small talk.

"Wait!" Ritchie said. "I have to get a picture to show my mama." There was a bit of light teasing, but soon, a Kodak was coming out and the group was all getting together. Sam stood off to the side. "Sam, what are you doing?" Ritchie asked as he got the camera set up.

"Waiting for you guys to get done." Sam said. JP shook his head.

"Come on, get over here." He said.

"But…" Sam started to argue.

"Sam, you're as much apart of this as everyone else." Buddy said. "Now get over here." Waylon reached out and grabbed Sam's hand, pulling him into the group. Once they were settled, Ritchie started the timer and ran to join the group. Once the flash cube went off, he pocketed the camera. He wanted to get it developed before the tour so he could have a fresh roll for the tour, and he could get some pictures sent out to his mom.

"Okay, are we gonna play or not?" JP asked.

"Yeah, yeah, we can play now." Ritchie laughed. "Who wants to go first?"

"How about the old man goes first?" Buddy teased, since he wasn't much older than Ritchie. JP glared him down. "What? Afraid you might break a hip?"

"I'll show you breaking a hip." JP grumbled as he got set up, ready to play "Chantilly Lace". Sam set back with Buddy and Ritchie, ready to watch the performance at hand.


	10. Chapter 10

**Warnings: Mild violence**

 **Present**

Dean was pacing as Cas sat cross legged on the bed, trying to find either the demon or Sam. As Dean paced though, he noticed for the first time the theming of the room. There were guitars and records on the walls. It was a very 1950's, rock & roll feel. How ironic.

"Dean." Cas said. Dean turned to look at the angel. "I can't sense Sam's soul, but I think I might have an idea where the demon is."

"Good. If we leave now and I don't drive the speed limits we might be able to catch it…" Dean said. Cas shook his head.

"The demon is here in Clear Lake." Cas told him. "I can't pinpoint his exact location, but I can tell that he's here." Dean sighed.

"I guess that's better than nothing." He said, rubbing his eyes. "And I think I might have a general idea of where to start."

"Where's that?" Cas asked.

"The museum Sam and I were at when he got DeLoreaned. We were trying to help a ghost move on. If Ritchie is hanging out there, then the demon must be around there."

"Do you want me to scope it out first?" Cas asked. Dean shook his head.

"No. If the demon knew we were coming, he can smell you from a mile away." Dean said. "I mean, we can just show up there after hours and see what we find."

"Why don't we ever break into someplace during business hours?" Cas asked. Dean smiled.

"Where's the fun in that?" He asked. "Come on. It'll be closing soon. We need to talk to Ritchie." Cas nodded and headed out with Dean to the Impala. It wasn't far from their hotel to the museum. Dean and Cas staked it out for a little bit, making sure that it was empty before they got out and slipped in through a side door. It was dark inside, but Dean was used to looking around in dark places.

"Ritchie." Dean whispered. "Ritchie, come out man." The building got colder and Dean looked as the ghost materialized in front of them. "Hey man."

"Dean? What are you doing here? Who's that?" Ritchie asked.

"This is Cas. He's going to help us. Get you to heaven and help me get Sam back." Dean explained. "Now, I need you to tell me where the demon is."

"Corson. That's his name. Y está por aquí en alguna parte." Dean looked at Cas as Ritchie started to trail off into Spanish. "Dean, ¿puedes oírme? ¿Hola?"

"Cas, I need some translation now." Dean said.

"Dean, está justo ahí..." Ritchie said, his panic making it hard for Cas to translate what he was saying. The jukebox turned on then, playing Patsy Cline's "Walking After Midnight". Ritchie hoped the music would get Dean's attention, especially if he knew his music history. But no such luck as Cas was blasted out of the building and Dean was hit upside the head when he turned to see what was going on.

"Oh Ritchie, what am I going to do with you?" Corson laughed, looking down at the unconscious Dean. "But you know I'm a sucker for musicians that died in plane crashes." He laughed and got ready to tie Dean up while Ritchie was forced to watch.

 **1959**

"Sam!" Buddy called up the stairs. "We're leaving soon! Are you ready?"

"Just a minute." Sam said, checking to make sure he had everything packed. They were leaving soon to fly out to join the tour. Sam had to remind himself that this wasn't the flight where Buddy died. It would be coming up later on. This flight was just fine.

Sam grabbed the bag he had packed and looked at the letter laying on the desk, Dean's name scrawled across it. He had wrote out a letter for his brother, just in case he didn't make it back to his time. He wanted his brother to get one last thing from him in case he never saw him again. He took the letter and headed downstairs where Buddy and Maria were saying goodbye to each other.

"I'll be home in February." Buddy told her, cupping her face and kissing her gently. "And I'll call you every night." Maria held back the tears that were coming. " _A-you're the one that I'm_ _thinking_ _of. You're the one that I'll_ _always_ _love. You're the one sent from_ _heaven_ _above. You're the one that's a-meant for me_." He sang to her as he held her close. She glanced over at Sam before resting her head on Buddy's chest.

"I love you." She whispered to him. He kissed the top of her head.

"I love you too." He smiled then looked over at Sam. "I'm gonna put the things in the car."

"I'll be right out." Sam told him. Buddy nodded and grabbed the bags, heading to the car. Sam walked to Maria. "I can try to save him, you know."

"You said it yourself. It could be disastrous." Sam nodded and handed her the envelope. "What's this?"

"If there is a chance I don't make it back to my timeline and see my brother, I want you to give this to him." Sam explained. Maria looked down at it then up at the hunter. "If I don't get out of this timeline, I'm gonna take up hunting again with Waylon. And hunters don't have a long shelf life."

"Sam…"

"Just do it, please?" He asked. She nodded and laid the letter on the small table before hugging Sam.

"I know you can't save him, but please come back." She whispered as Sam hugged her. "I don't want to do this alone."

"You won't be alone." He pulled away. "I better go or Buddy might leave me behind."

"You be careful Sam." She told him. Sam nodded and left, catching up with Buddy who was waiting at the car.

"God, I already miss her." Buddy laughed. "Is it too late to cancel?"

"I think so yeah." Sam joked. Buddy got in the car and they drove off to the airport, ready to start the tour.

"Dear god, this was a mistake." Buddy said, rubbing his hands together. "Sam, why didn't you stop me from agreeing to this?"

"I have no control over it." Sam buried himself deeper in the coat he was wearing. It was the early morning hours of February 2nd. They had stopped the tour bus a couple times because JP had to throw up. Poor Ritchie was out of his element. He was used to warm, California climate.

"I hope my fingers thaw out before I have to play again." Waylon said, moving his fingers to keep the blood flowing. "Crappy tour bus."

"We're almost to Clear Lake." Someone said. "We can all warm up and sleep then." Sam closed his eyes and took a deep breath.

Countdown to the end.

Buddy's part of the concert was over and he had disappeared backstage to talk to Maria. He hadn't talked to her in twenty-four hours and god he missed her. But it was taking longer than normal.

"You think Buddy's okay?" Sam asked, leaning over to talk to Waylon so he could hear him.

"I'm sure he's fine. Probably got a little worked up talking to his girl." Waylon teased. Sam shook his head and headed towards the bathroom backstage. As he made his way to the bathroom, the light from the dressing room Buddy had been using shined into the hallway. Sam pushed open the door, ready to talk to him.

And that's when he saw Buddy plunge a knife into his side.

"Buddy!" Sam yelled, grabbing the knife away from him. Buddy turned to look at Sam.

"You weren't supposed to see that Sammy." He said, his eyes turning black.

"No." Sam said. "Get out of him."

"Why would I do that?" He laughed. "It's a very comfy fit. Just like a well tailored suit." Sam got ready to start an exorcism, but Corson shook his head and punched Sam hard in the side of the head, knocking him to the ground.

"You're not going to stop me Winchester." Corson said, blinking so his eyes turned back to normal. "Come on Sam, we have a plane to catch."


	11. Chapter 11

**Warnings: None**

 **AN: Thank you to everyone who read this! Also, a big shout out to my friend who translated Ritchie's dialogue into Spanish for me. If you have any ideas that you'd like to see, just let me know!**

 **Present**

"Dean. Dean. Despierta. Vamos, sé que estoy hablando en español pero tu nombre no es diferente en mi idioma." Ritchie said, hovering around Dean who was tied to a desk chair. Dean started to wake up, groaning as he did. "Gracias a Dios."

"Ritchie?" Dean asked, groaning some. He was really surprised that Sam didn't have more permanent brain damage from getting knocked out so much. It was painful and unpleasant...and he had done his fair share of knocking his brother out before.

"Temía que Corson te matara." Ritchie said. He knew Dean couldn't understand him, but he always talked when he was nervous. Dean looked around, hoping that Cas could bounce back quickly from being blasted away, but no such luck.

"Ritchie, where is Corson?" Dean asked.

"I'm right here Dean." Corson said, strutting up to Dean. "You were playing with my toys, that's not very nice."

"Hijo de perra, si pudiera matarte, lo haría. Espero que Dean te mate. Espero que sea doloroso y..."

"Ritchie, shut up." Corson said, looking back at the ghost. Ritchie instantly couldn't talk anymore. Dean looked between him and Corson.

"What did you do to him?" He asked. Corson laughed.

"The same thing I've been doing to him since 1959." Corson pulled up another chair to sit down in front of Dean. "It's actually quite fun. You should try it sometime."

"Why him?" Dean asked. Corson shrugged.

"Wrong place at wrong time." He said. "I took JP Richardson's soul because he sold it. So that was my first golden ticket. Then watching Buddy Holly die without his "true love" Maria, that was number two. I knew she was pregnant, I just didn't know that his death would hurt her so bad. Considering I snagged her from the 90's in the first place, trying my hand out at time travel." He laughed. "So what was I supposed to do with poor little Richard Valenzuela? I like torture after all. So I decided that it would be best to keep him trapped here, as a ghost of course. Tied to the town he died at. He has to watch as everyone he ever knew and loved grew up and moved on. He had to watch as the world changed around him. Seventeen years old and in love, and he can't even do anything about it."

"God, you're one sick son of a bitch." Dean growled.

"I wanted to get Waylon Jennings on the flight, cut that career before it even started, but that drummer Sam Winchester walked in on me at the wrong time. So of course he had to die."

"You killed my brother!" Dean shouted, pulling on the restraints.

"At first, I didn't know he was your brother. I was just going off of Buddy's memories. After I dumped him on the plane and high tailed it out of there, I realized who he was, from the prophecies and the plans that Azazel was talking about." Dean just stared the demon down. "Now now, don't worry. I bet he didn't feel a thing when he hit the ground. I'm sure none of them felt it when they were thrown out of the plane." Corson laughed.

"I am going to kill you." Dean said in a low, more threatening voice.

"I'd like to see that." Corson patted Dean's knee as he stood up. "But you see, you're nice and tied up. And all I have to do is tell Ritchie here to kill you, and you're dead."

"You don't know me and my brother very well, do you?" Dean asked. "We don't like to stay dead."

"Oh, I know all about that. But I have confidence that this time, you won't be coming back." Corson smirked. "I have strings that I can pull and suddenly Dean and Sam Winchester are no more."

"¡Es suficiente!" Ritchie screamed, breaking through Corson's spell. Corson turned to look at the ghost when Ritchie attacked him. Dean's eyes widened as he watched the wrestling match between the ghost and the demon. The doors flew open then and Cas walked in. He immediately went over to Dean, touching the ropes on his arms and making them fall away. Dean stood up, knife in hand, as Corson threw Ritchie off of him. Cas grabbed the demon, holding him still, while Dean stabbed him in the chest.

Yellow and orange danced under the skin of the body he was using. Once it stopped, Cas dropped the body to the floor. The angel and the hunter looked at each other before looking over at Ritchie.

"Ritchie? How do you feel?" Dean asked.

"Light." He said. His eyes widened, realizing he was speaking in English. "What do I do?"

"Just relax and let yourself move on." Cas said. Ritchie closed his eyes and he started to flicker, but a warm light surrounded him. When the light disappeared, so had Ritchie.

"Well, two things down, one more to go." Dean said. "Cas, go get Sam." Cas nodded and this time, he disappeared, leaving Dean standing in the middle of the museum.

 **1959**

Sam groaned as he came to, confused to where he was. It was a little bathroom, very cramped. He rubbed at his head, trying to ease the pain, when the room he was in gave a rough jerk. He managed to find the door then and opened it to show he was on an airplane.

"No." Sam whispered, looking around. He saw Ritchie and JP sitting, looking terrified. And that's when Buddy came out of the cockpit, a wicked smile on his face.

"Don't worry Sam. I'm leaving." With that, his head threw back and black smoke flew from his mouth. Buddy's body fell to the ground, blood leaking from his mouth. Sam ran to him while looking up into the cockpit. Roger Peterson sat in his seat, head leaning back from his throat being slit. The dashboard was completely destroyed, so even if Sam could figure out how to land the plane safely and save them all, he couldn't.

"S-Sam." A low voice said. Sam looked down at Buddy. He was coughing on blood and his eyes were half closed, but he was still alive. He wasn't dead like the demon had thought he was. "A-are w-w-we going to d-die?" Sam just closed his eyes and held his hand tightly. He heard a choked cry come from Ritchie. He reached out and held his hand. He looked up at JP for a second.

"I'm so sorry." JP whispered. Sam looked away from him and closed his eyes again, holding onto Buddy and Ritchie as he started to hum, trying to keep himself calm before he died.

"Sam!" A familiar voice said before behind him. Sam's eyes snapped open to see Cas standing there. He walked to Sam and grabbed his arm, pulling him away from Buddy and Ritchie.

"S-Sam!" Buddy called out, reaching for him. But Cas held on to him and took him away.

Right as the plane smashed into the ground.

 **Present**

Dean was pacing in the motel room, waiting for Cas to come back. He had just turned the other way when he heard what sounded like feathers rustling. He spun around to see Cas standing there with a visibly shaken Sam. He had blood on him from Buddy, a bruise on his forehead, but he was alive.

"Sammy." Dean said, crossing the room quickly and wrapping his arms around his brother. After a moment, he pulled back to examine him. "Is that your blood?"

"No. It's Buddy's." Sam said.

"Buddy? Like Buddy Holly?" Dean asked. Sam nodded and looked over at the table, seeing his letter and the photos laying there.

"I see you met Maria." Sam said. Dean nodded.

"She helped a lot." Dean was still giving Sam and visual once over. "Are you sure you're okay?"

"I…" He sighed, wanting to say that no, he wasn't fine. He had just watched someone he had grown close to die by the hands of a demon. "I'm fine." Dean didn't believe him, but he didn't question it. "How did Cas get back there?"

"We killed the demon holding onto Ritchie and were able to get back to you." Dean explained.

"That demon possessed Buddy and caused the plane to crash." Sam explained. "JP sold his soul." Dean nodded and went over to their bags, packing. "What are you doing?"

"I want to get the hell out of this town. I think we can go home." Dean didn't look at Sam as he packed, because in his mind, he was still seeing that newspaper article that showed that Sam had died right along with the others. Sam went to the bathroom to wash the grease out of his hair real quick. He wasn't sure if Dean had seen it or not, but he didn't want to give him the chance. Plus, he doubted he could handle it being in his hair all the way back to Kansas.

Once Sam was done, they packed up and got into the Impala. Cas had disappeared off to who knows where. But Dean really couldn't care any right then. He just wanted to go home with his brother by his side. He started up the car, the radio turning on.

 _Bye, bye Miss American Pie_

 _Drove my Chevy to the levee but the levee was dry_

 _And them good ole boys were drinking whiskey and rye_

 _Singin' this'll be the day that I die_

 _This'll be the day that I die_

"Crap. I'll turn that off." Dean said. Sam shook his head.

"No, it's okay." Sam said, settling back in his seat. A smile spread on his face as he remembered the good times. He had only been there for three months, hanging out with Buddy, Maria, and Waylon. Eventually, he would tell Dean about everything that he had done and seen in those months, but for now, sitting back in the Impala beside Dean while Don McLean sang about his friends, well, Sam couldn't ask for more.

 **END**


End file.
